


The Courtship of Edward Kaspbrak, Executive Asshole

by teafortozier



Category: IT (Movies - Muschietti), IT - Stephen King
Genre: Alternate Universe, Alternate Universe - No Pennywise (IT), Alternate Universe - Office, Dating, Eddie Kaspbrak Loves Richie Tozier, Established Relationship, Fluff, Gay Richie Tozier, M/M, Marriage Proposal, Office, POV Original Character, POV Outsider, Richie Tozier Loves Eddie Kaspbrak, Romance, They're Both Insufferable But Not To Each Other, Tooth-Rotting Fluff, Unlikely Pairs
Language: English
Status: Completed
Published: 2020-07-06
Updated: 2020-07-06
Packaged: 2021-03-04 22:42:17
Rating: Teen And Up Audiences
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 3,505
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/25104121
Author URL: https://archiveofourown.org/users/teafortozier/pseuds/teafortozier
Summary: Two weeks into her new job as Executive Assistant to the world's most anal-retentive, pent-up ball of pure fury and finance expertise known as Mr. Edward Kaspbrak, Lucy thought she was coming to grips with her boss's particular brand of crazy. Edward was in his office reaming some poor associate for “desecrating the carefully organized sanctity of his spreadsheets” the first time she encountered Richie Tozier.When he walked up to her desk with two bursting bags of takeout, wearing a “Nobody Knows I’m Gay” t-shirt under a garish yellow short-sleeved button up with a pattern of little dinosaurs across it, and old Converse sneakers with the soles falling out from under him, Lucy almost called security.“Why, hello, Madame Secretary,” he said. “I’m looking for Mister Eds Spagheds.” He flourished the takeout bags with a little bow. She recognized the familiar logo of Edward’s favorite Thai place, the one that was across town that she had to pay an Uber Eats guy double to venture out to, because her life was a nightmare.
Relationships: Eddie Kaspbrak/Richie Tozier
Comments: 20
Kudos: 485





	The Courtship of Edward Kaspbrak, Executive Asshole

**Author's Note:**

  * For [tranquilatlast](https://archiveofourown.org/users/tranquilatlast/gifts).



> I saw [this tweet](https://twitter.com/kaspbrave/status/1279350364303552515?s=20) and couldn’t stop thinking about an outsider pov of uptight edward kaspbrak being a lovestruck fool for the goofiest idiot around, and the sort of duality of office asshole/road rage eddie vs soft in love eddie and so i wanted to write a couple scenes from it. 
> 
> (also, writing edward in reddie felt way weird but i wanted to be deeper in lucy’s pov so i’m dealing with it and i hope yall do too)

Lucy pressed submit after the arduous process of punching in Edward Kaspbrak’s lunch order, having meticulously detailed which items should be on the side, or excluded, or extra, or prepared separately for sanitary purposes, with a note at the end threatening murder if there were any mistakes or shortcuts, and _yes_ , they would know. Each day she cursed herself for making the idiotic decision to major in Philosophy in college, and every other decision that led her to the hellscape that was her life as executive assistant to the most neurotic workaholic in the world. 

Mr. Kaspbrak, as she called him to his face, or Edward, as the office referred to him behind his back, had a stick set up permanent rent-free residence up his ass. He was currently in his office reaming some poor associate for “desecrating the carefully organized sanctity of his spreadsheets.” 

Lucy shook her head at the poor guy’s ignorance. She’d learned on day two on the job how particular Edward was about literally everything, from his coffee order--which he expected on his desk when he got in at seven-fifty-nine sharp each morning--to the color of pen she used in her memos--blue was “unprofessional for the workplace,” apparently.

Across the hall, another long-suffering EA, Eve is raising her eyes in a dramatic eye roll, generously co-miserating from her station. She’d been here to witness two years of Kaspbrak meltdowns, watching assistant after assistant fail to meet Edward’s expectations until they either quit or got replaced. She was a good assistant, but had been working for a slightly more stable (but far more boring) senior executive something-or-other.

Lucy had only been working for Edward for two weeks, but in that time, she’d never seen the guy anywhere approaching “friendly.” Lucy wasn’t convinced he existed outside of the office, where his brows were pinched in a permanent frown and he rubbed his temples at everyone’s incompetence, with his tie done up and his clothes impeccably ironed. He’d never mentioned a social life, and Lucy could only assume he didn’t have one. She couldn’t imagine him hanging out with anyone, or relaxing.

So when the comedian Richie Tozier walks up to her desk with two bursting bags of takeout, wearing a “Nobody Knows I’m Gay” t-shirt under a garish yellow short-sleeved button up with a pattern of little dinosaurs across it, and old Converse sneakers with the soles falling out from under him, Lucy almost called security. 

“Why, hello, Madame Secretary,” he said. “I’m looking for Mister Eds Spagheds.” He flourished the takeout bags with a little bow. She recognized the familiar logo of Edward’s favorite Thai place, the one that was across town that she had to pay an Uber Eats guy double to venture out to, because her life was a nightmare.

Lucy arched a brow and in the beat she took to consider responding, Edward’s voice raised in the office _“--it’s not so much to expect a certain level of competency--”_

Richie Tozier-- _the comedian??_ her mind piped up helpfully, trying to connect dots in her head--grinned at the sound, a private little smile, like he was enjoying the dulcet tones of some kid getting roasted for not knowing how to use Excel.

“Um, what?” Lucy finally said.

“Sorry, I’m here for _Eddie_ ,” he corrected, as if he was corrected on that often.

“Edward...” she said this slowly, because, _Eddie?_ Who the hell called him Eddie? Past assistants had gotten fired for less. “...is in a meeting right now. Do you have an appointment?”

Richie laughed, warm and familiar, and Lucy felt her frown deepen. She spared Eve a glance across the hall, who was watching on and laughing too. She got the distinct feeling she was missing the punchline to a joke. 

Behind her, Edward’s door clicks open and the associate, a generic young-professional-with-Daddy’s-money type, slipped out the door with his tail between his legs like he’d been awaiting his opportunity to flee. Behind him, Edward Kaspbrak’s less-than-six feet of pure rage filled the doorway. 

“Eds!” said Richie Tozier, lighting up like a puppy. Lucy watched Edward’s eyes fall on him and the tension in his shoulders relaxed instantly in a way she’d never seen before. Her mind was spinning. _Eds?_

“What are you doing here?” Kaspbrak asked, crossing to Richie in a few long strides like he couldn’t move fast enough, and put a hand on Richie’s arm. Lucy bowed her head to bury her nose in her planner, making herself look busy. 

“Can’t I surprise my boyfriend on his lunch break?”

Lucy cleared her throat to cover the way she almost choked on nothing in surprise. This asshole with big dorky glasses who may or may not own a hair brush was _Edward Kaspbrak’s_ boyfriend? 

Edward brought a hand to rub at his own temples and said, “I’m all--out of sorts. It’s been a busy day.”

“Too busy for Thai?” Richie asked, then, in a southern accent and with as much of a swoon as he could muster with his hands full of takeout, “Or lil’ ol’ me?”

Edward’s face went weird and did something she’d never seen before, him pressing his lips together all tight before she realized he was _smiling_ , or rather, trying _not_ to smile and failing miserably. 

“I can’t say no to Thai,” Edward finally agreed, and let his smile take over his face, and he suddenly seemed a lot less like a scary entity and more like, well, a person. He took one of the takeout bags and said, “I suppose I’ll put up with you if I have to.”

He turned back toward his office, hand sliding down Richie’s arm to link hands and drag him along. Richie trailed behind with a lovesick smile and Lucy blinked on in disbelief long after the door shut behind them.

She must have been making a face, because Eve pinged her on Slack from across the hall. 

Eve > Lucy:  _my favorite part of edward’s parade of assistants is getting to watch each of yall react to richie tozier_

Lucy blinked at her monitor, then looked back over her shoulder at the closed up office, the window shades always closed and private to keep her from confirming whether that had all really happened. 

She shook her head, and started typing and clicking madly to try to cancel her boss’s lunch order before it was too late. Once it was done, she returned to her bewilderment and typed:

Lucy > Eve: _He called him Eddie???? And Eds???? He smiled????_

The response came fast.

Eve > Lucy: _I’d like to say you get used to it, but you really don’t_ 😂

Lucy definitely didn’t think she’d get used to that.

An hour later, Edward literally pushed Richie out the door of the office, still laughing and insisting he had work to do. Richie held the door open with one hand splayed across the wood while Edward had a defiant set to his jaw. Lucy tried to make it look like she was studying her monitor instead of paying attention, trying to understand the situation that led to this pair being a functioning couple. 

“I’ll think about it,” Edward said, and then tugged Richie in by the collar for a kiss that wasn’t completely brief and work appropriate, in her modest opinion, Richie’s hands going to his waist and face with practiced ease. 

Lucy didn’t think she’d ever seen Edward, like, _relax_. He was always gearing up to yell at somebody, or rushing from meeting to meeting to kiss people’s asses. But when Richie finally pulled away and slinked off with a lazy salute-wave to both Lucy and Edward, Lucy said goodbye and politely ignored the way Edward was blushing, lingering in the doorway with a grin she could only describe as lovetruck.

An hour later, a memo appeared on their shared to-do list organizer, in the section for Edward’s notes to himself for the day. There was a memo that said, “apologize to associate from mktg for ‘berating’ (richie’s words not mine)” and then a frowny face. 

Frowny face, indeed. Lucy hadn’t been convinced before that Edward knew how to apologize, and certainly didn’t know when to. But, she guessed, there was a lot she didn’t know about him.

  
⋅•⋅⊰∙∘☽༓☾∘∙⊱⋅•⋅  


Two weeks after Lucy first encountered Richie Tozier, she was combing through Edward’s calendar, which was color-coded and perfectly filled up to the minute, trying to find two hours in an evening for him to attend a dinner with some corporate bigwigs.

To Lucy’s bewilderment, Edward Kaspbrak seemed to have an insultingly bustling social life, as she learned once she gained full access to his personal calendar on week three on the job without getting fired. Although she could barely imagine the uptight man having friends, almost all of his evenings were blocked off with long boxes, color coded blue for “Losers,” which Lucy didn’t understand and Edward never explained. He had weekly recurring appointments labeled “call with stan” and “Brunch with Bev and Ben” and “dinner with Bill and mike” and “Losers Skype call” and, overwhelmingly, blocks just labeled “Richie” with no further details. 

The lack of details was what really alarmed Lucy about the Richie Tozier calendar blocks. Each lunch date had the name of a restaurant with the address, reservation information, and notes about what dishes he liked best. Each phone call had a phone number and, sometimes, notes to himself about things to talk to them about, or links to videos to share with them. It was almost cute, if that were a word Lucy would associate with her boss. 

She grumbled in frustration and minimized the calendar, and drafted a quick message to Edward, who was in a presentation with some junior analysts downstairs for the next hour. 

Lucy > Edward Kaspbrak: _Mr. Kaspbrak, I need to fit in a meeting with the executives from Greenwell. They’re looking at the evening of the 13th. Is your “Richie” calendar block flexible?_

She’d yet to fuck up enough to really face Edward’s wrath, but she’d witnessed it enough to know she didn’t want to deal with it. She returned to her other work for a moment, not expecting a response any time soon, but after only a minute she got a ping.

Edward Kaspbrak > Lucy: _Blue calendar blocks are non-negotiable. I’ll rearrange for the 12th 5-7pm._

She looked at his calendar, where he’d have to move two meetings to make it work. But she wasn’t about to argue with him.

Lucy > Edward Kaspbrak: _I’ll make it happen_ , she replied instead, and started emailing the necessary parties to reschedule some other meetings. 

Then she messaged Eve again. 

Lucy > Eve: _I think he has???? work life balance????_

Eve > Lucy: _absurd. illegal. call hr immediately._

Lucy > Eve: _I’m just surprised. I wouldn’t have expected it._

Eve > Lucy: _ikr its hard to believe the tinman has a heart 🙊_

At the same time, another response came from Edward. She expected an extra note or request, maybe a coffee run. Edward wasn’t one for pleasantries, wouldn’t waste time with small talk or Slack gossip like normal people. 

But this was the message:

Edward Kaspbrak > Lucy: _Thank you._

In three weeks, this was exactly the third time Edward had thanked her. The other two were on mornings when he’d accepted coffee from her with bleary eyes and heavy exhaustion, like he was too tired to even realize he was saying it. But this was a fully-awake, fully sentient, intentional Edward Kaspbrak _thank you_. Lucy nearly threw a fist in the air.

  
⋅•⋅⊰∙∘☽༓☾∘∙⊱⋅•⋅  


If Lucy thought her life as Edward’s assistant was a hellscape before, she was living in the universe of Dante’s inferno, and had just fallen a level deeper into hell. The whole last two weeks had been slammed, a bunch of deadlines for a lot of clients quickly approaching, meaning Edward’s schedule was even more packed, the man himself far more uptight, working through lunch and staying late, while Lucy scrambled to keep everything in order to make his life as easy as possible. Currently, that meant harassing a couple of associates via email on his behalf to get their work done while Edward was yelling down the phone in his office.

This time, when Richie Tozier walked up to her desk in an eyesore of a jacket and jeans with holes in the knees, she cringed. As much as the man seemed to calm Edward, she had a feeling even Richie would get his head ripped off if he interrupted his jam-packed schedule. Just an hour ago, Edward had been on a rant to Lucy about managing the schedule:

“It’s a perfectly designed system, by the minute,” he’d said fiercely, chopping a hand down into the other one for emphasis. “If I’m delayed even a minute, the work we need to get done will not get done. What does that mean?”

“No delays,” Lucy had repeated back dutifully. 

So now, Lucy was warning, “Look, Richie, he’s developing a stress ulcer in there--” 

“Lucy!” Richie greeted warmly. He’d come to visit Edward a few more times since Lucy had been working here, and he always made an effort to say hi and chat a bit before dragging Edward to get food or disappearing inside his office with takeout. “How’s my favorite assistant to my favorite Eddie?”

Each time she met Richie, she wondered how the hell a relationship between the guy and Edward could possibly work. It wasn’t her business, really, but she couldn’t help but wonder. Was it a hostage situation? _Blink twice if you’re here against your will._

“I’m fine,” Lucy dismissed. “Your boyfriend, however…”

Richie brought his hand up in a crisp military salute and said, in a voice similar to an old-timey spy who wore suits and sported a mustache, “Lieutenant Tozier, on the job. They all say it can’t be done but dammit if I won’t try!”

Lucy really didn’t know how to interact with Richie, so she just said, “Um, right.” 

“Oh come on, Luce, play with me once in a while!” Richie said. He said this a lot. He’d say, _play with me! Do a little_ yes-and _with me, Lucy-Goosey._

Lucy gave him a withering look which he met only with an easy smile. She rolled her eyes and waved him past. “Go ahead,” she said, “but don’t say I didn’t warn you.”

She expected Richie to be sent packing within a minute, or five, max. Instead, ten minutes past as Lucy tried to focus on her work instead of on eavesdropping on her boss. Edward had hung up, and now she could hear Richie talking and Edward laughing. She could count on one hand the number of times she’d heard Edward laugh, and, now that she thought about it, all of them had been when Richie was in the office. 

Another five minutes later, they both emerged from the office with their jackets on, Edward with his satchel which Richie had jokingly called a “modern fanny pack” on multiple occasions. 

“I’m taking lunch,” Edward said, like it were no big deal, as if he hadn’t been skipping his lunch breaks for the last two weeks, and Lucy worried until he added, “If I’m not back in forty-five minutes on the dot, call the police, it’s a hostage situation.”

Lucy had the urge to pull out her hair as she started thinking about all the phone calls she’d have to reschedule to buy him even one hour, but she gritted her teeth in what could possibly pass for a smile and said, “Enjoy your lunch, Mr. Kaspbrak.”

Richie snorted, which he always did when someone called him Edward or Mr. Kaspbrak, and they both left. Lucy took a minute to push her hands in her hair and groan in frustration before getting to work moving things around.

Even if it was annoying, she had to admit the guy deserved a break. If anything, she knew he’d come back from being with Richie a little brighter. 

An hour and fifteen minutes later, he returned with a smile, and a pastry from a coffee shop for her. Her jaw nearly dropped when he set it on her desk as he breezed past toward his office to hop onto a conference call he was late for.

  
⋅•⋅⊰∙∘☽༓☾∘∙⊱⋅•⋅  


When over-the-top bouquets of flowers started getting delivered for increasingly bastardized versions of the name Edward, Lucy knew it was Richie Tozier’s fault and went ahead and waved the delivery guy in to interrupt the guy from whatever he was doing. Her boss who hated interruptions, she had learned, didn’t mind interruptions so much when they had to do with his boyfriend. When he saw the flowers he just let out a hearty laugh and spent the next fifteen minutes on the phone ignoring his emails and he was smiling which, again, meant Richie.

Sometimes, Edward would walk in his office and past her desk in the morning with a pep in his step, looking like he’d actually gotten some sleep, and he’d say good morning to Lucy, or even thank her for the coffee she got for him every day. She was starting to believe _that_ had something to do with RIchie too. 

All this to say, by the time Lucy had been Edward’s assistant for six months, Richie Tozier felt as much a part of the job as Edward did, or the line at the good coffee place across the street, or the different timers she had set for Edward’s pills, vitamins, and, on busy days, bathroom breaks. (Being an EA was like being a babysitter in more ways than one.)

So when Richie came to surprise Edward for lunch again, there was nothing out of the ordinary about it. Richie looked like he always did, wearing too-bright and too-worn clothes and a goofy smile, holding a couple of unmarked bags. Lucy waved him right in nowadays, or if Edward were busy, pinged him so he could get rid of whoever was in his office. 

But what _was_ different was this: before he threw open the door, he looked over his shoulder at Lucy and said, “Here goes nothing.”

The door closed behind him with an ominous finality to it and Lucy started running through emergency protocols in her head, and ended up pulling up her always-lingering chat window with Eve. 

Lucy > Eve: _i think richie’s about to break up with edward_

Eve responded with a series of exclamation points and a couple of vague yet somehow vulgar emojis. Lucy caught her eye from across the hall and Eve started gesturing, waving at her with _go on_ gestures and Lucy didn’t hesitate to bolt out of her seat and over to the door, for once grateful for the closed blinds so she could listen in without being seen.

Except, for once, Richie wasn’t talking in his loud, exuberant way, making Edward let out loud, sharp laughs or sending him spiraling into a warmer version of his typical tirades. She felt like a kid, pressing her ear to the door, but she held her chin up and did it with dignity, listening to the foggy sound of hushed voices. 

“Eds,” she heard a couple times, the only thing she could really make out. That still nearly wiped her out every time, that the uptight Mr.-Kaspbrak-Sir was apparently a softy for the goofy lanky guy with weird nicknames.

Lucy frowned and mouthed across the room to Eve. _They’re not fighting_ , she said, or tried to. Eve probably didn’t get the message based on how she continued to type furiously at her work station, while Lucy’s desk beeped at the flood of incoming messages. 

Lucy looked between the door, where she was getting no extra insight, and the laptop, where she was getting a stream of consciousness direct from her cute coworker, and scurried back to her desk to check the responses. But she couldn’t even reach the desk before the sound of Richie’s voice boomed out of the room with joyful abandon--

_“WE’RE GETTING FUCKING MARRIED!”_

\--followed by a loud whoop cut off by a crash that sounded like a chair, a human body, and a number of books falling to the ground. Lucy swiveled back to the door, nearly bursting into help before she heard one final, loud noise that clarified things for her.

Someone--no, not someone, it was unfortunately and unmistakably Edward Kaspbrak--moaning. Then a wet sound, another crash, and then a grunt. 

Lucy sprung into action. If there was one thing she could do, it was reading the goddamn room. So she let her boss fuck his fiance and started clearing his schedule for the day. It sounded like the guy would need it. 

  
⋅•⋅⊰∙∘☽༓☾∘∙⊱⋅•⋅  


By the end of the week, Lucy’s gotten an email from HR about a raise, and found on her desk an expensive gift basket of artisan wine, organic vegan chocolates, fruits and nuts, topped with a handwritten note from her boss that said:

_You’re the best assistant I’ve ever had.  
Eddie_

**Author's Note:**

> i just like the idea that eddie seems super cold and demanding but what makes lucy the best assistant is that she sees what he cares about and understands his priorities are his family and richie and she works around it okay 
> 
> ((did anyone sense the gay tension between eve and lucy? i wanted to write in a subplot but didnt want to go crazy into OC territory. but if ur wondering, yeah, harold, they’re lesbians.))
> 
> pls come talk to me on twitter [teafortozier](https://twitter.com/teafortozier)


End file.
